Decanal → 4-Bromo-N-decyl-3-(trifluoromethyl)aniline

HRID 1250006

Reaktionsgleichung

Reaktionsgleichung von HRID 1250006
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:15][C:16]([F:26])([F:25])[C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][C:23]=1[Br:24])[NH2:20].[CH:27](=O)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>CO>[CH2:27]([NH:20][C:19]1[CH:21]=[CH:22][C:23]([Br:24])=[C:17]([C:16]([F:15])([F:25])[F:26])[CH:18]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Komponenten

5

Edukt 3

HCID 8175DecanalHCID 678524-Bromo-3-(trifluoromethyl)anilineHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 183293104-Bromo-N-decyl-3-(trifluoromethyl)anilineAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (4 g) was added to a solution of 3-trifluoromethyl-4-bromoaniline (1.5 g) and decanal (4 mL) in methanol (90 mL). After stirring for 1 h the solution was partitioned between water and petroleum ether. The organic extract was concentrated under reduced pressure and the residue was purified via flash column chromatography using petroleum ether as eluent to give N-Decyl-4-broma-3-trifluoromethylaniline (4) (1.2 g, 53%). 1H NMR (CDCl3) δ 7.44 (d, 1H, ArH); 6.92 (d, 1H, ArH); 6.61 (dd, 1H, ArH); 3.11 (t, 2H, NCH2); 0.80 (t, 3H, CH2CH3). TLC (silica gel): Rf=0.35 (petroleum ether).

Aufarbeitung

  1. customwas partitioned between water and petroleum ether
  2. extractionThe organic extract
  3. concentrationwas concentrated under reduced pressure
  4. customthe residue was purified via flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4d1099398ca04c12a86d0297e07674de
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06335446B1

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